Let’s jump straight in, buckling up for some old favorites and a couple of moves you probably didn’t see coming.

Max Out Your Tax-Advantaged Accounts

Look, I know. It’s not a new gizmo or a glitter bomb. It’s just the tried-and-true: max out your tax-advantaged accounts. But sometimes the basics are classics for a reason, like pizza or sweatpants with pockets.

Why These Accounts Matter for High Earners

This move packs a punch because for every buck you sock away, you get both tax deferral and potential savings. That means your money grows without the IRS grabbing a chunk each year, and you could avoid the nosebleed tax brackets when you put these funds away right.

Here’s the deal: By “save,” I mean “defer.” You hold off on paying taxes now, letting those dollars marinate quietly for decades. When you take the money out, the tax goblins will show up. But if you play your cards right, you might end up paying a lot less than you would today.

Which Accounts Should You Be Feeding?

Every tax-advantaged account has its own quirks. Here’s your hit list:

• 401(k) & 403(b): The old faithfuls. These let you tuck away a big chunk of pre-tax income. And if you have both, fill them both up if you can.
• 457(b): For you lucky ones in certain hospitals or government circles. Watch out though—there’s a government version and a non-government version, and they play by slightly different rules.
• Health Savings Account (HSA): Triple threat. You get a tax deduction up front, tax-free growth, and tax-free use if spent on qualified medical expenses. HSAs are so powerful, they almost feel illegal (but aren’t).
• Backdoor Roth IRA: For high earners walled off from normal Roth contributions, this is your legal side door. Put after-tax dollars in an IRA, then convert to Roth. No income limit roadblocks.
• 529 College Savings Plan: This one is a slippery little creature. No federal deduction, but state tax breaks and tax-free growth for college costs make it a no-brainer for future tuition monsters.
• Solo 401(k) / Mega Backdoor Roth: Earn 1099 income? These let you stack up massive retirement savings on the side. The Mega Backdoor Roth is a unicorn; not everyone has access, but if you do, get on it.

Quick Table: Common Tax-Advantaged Accounts for High Earners

Account	Main Benefit	Who’s Eligible	Tax Notes
401(k)/403(b)	Tax deferral	Employees	Big annual limits
457(b)	Extra tax shelter	Certain gov/hospital workers	Gov vs non-gov flavors, know yours
HSA	Tax-free triple win	Anyone with a high-deductible plan	Both tax deduction and tax-free use
Backdoor Roth IRA	Tax-free growth	Income too high for Roths?	Convert after non-deductible IRA
529 Plan	State tax benefit	Anyone saving for college	Tax-free growth, not federal break
Solo 401(k)/Mega	High contribution	1099/self-employed	Huge pre-tax or Roth options

Who Should Bother?

If you’re rolling in the high 20s, 30s, sometimes nipping at 37% on your tax bracket, this applies to you. That includes virtually all physicians, many dentists, veterinarians, business owners, and side-hustle warriors stacking both W-2 and 1099 pay.

And don’t forget—every time you pop an extra dollar into one of these accounts, you could save up to 37 cents on every dollar in taxes today. Why donate that to Uncle Sam when you can keep it compounding?

Don’t Sleep on the Basics

You’ve heard it before, but I’ll say it louder for the people in the back: This is where the real money piles up. It may not make headlines, but this is the concrete mixed right into your financial foundation.

One caution: Remember, this is tax deferral, not pure savings. You’re setting up future-you for a big bite later—unless you get clever with Roth conversions (which we’ll dig into in just a bit).

Understanding and Implementing Tax Loss Harvesting

Maybe you’ve heard “tax loss harvesting” and thought, “Sounds like farmer talk.” Well, you’re not far off—you’re planting a loss now to reap a tax benefit later. This move is the magic trick in your tax planning tool belt, and, for high-income folks, it’s as close to a cheat code as you get in real life.

What Exactly Is Tax Loss Harvesting?

Let’s keep it simple: You sell investments that dropped in value, locking in those paper losses. Those aren’t just virtual sad faces. You can actually use real losses to cancel out real gains—plus you get to offset up to $3,000 of regular income annually. That means you take a losing stock or fund, let it go, and Uncle Sam lets you use that hurt to soften the tax blow from something else.

This is what we call tax arbitrage—shifting losses to where they help you most. And in a high marginal tax bracket, every $3,000 loss harvested could mean putting over a thousand dollars back in your wallet each year. Yes, it adds up.

Watch for the Pesky Wash Sale Rule

Here’s the pitfall: Sell something at a loss, then turn around and buy the same thing (or anything substantially identical), and the IRS waves the magic no-deduction wand. That’s a wash sale. Don’t do it. Choose something close, but not the same—there are clever swaps out there that work, just stay on the right side of the rules.

Remember: No “selling everything to the ground and rebuying instantly.” Have a system. Make swaps with care.

Timing: Don’t Wait for the Holiday Rush

Tax loss harvesting is not a Christmas Eve activity. You want to start running your numbers in the fall—think October or early November—so you have enough time to swap, set, and forget before the year ends. Plus, who wants to spend the holidays thinking about ETFs and cost basis?

Now, while you’re at it, keep an eye on tax gain harvesting too. That’s the mirror image strategy for years when capital gains rates are (or could be) going up. This isn’t the year for that, but file it in your back pocket for future crazy tax code years.

Bottom Line

Tax loss harvesting is not fancy. It’s fundamental. It’s like flossing, but for your investments, and you get a tax break instead of icky gums. Keep a system. Review regularly. Don’t get greedy.

Charitable Giving Strategies to Maximize Tax Benefits

If you’re the type to write a check to your favorite charity each December, pat yourself on the back—you’re making the world better. But if you’re still taking the standard deduction (and most people are), you’re not getting an extra tax break for that gift! Bummer, right?

Here’s how you can make your generosity work double time—and actually see some love on your tax return.

Why the Standard Deduction Killed Your Charitable Break

In recent years, the standard deduction shot up. That means most folks just take that flat deduction, and their good deeds don’t lower their tax bill anymore. To get that juicy write-off back, you need to itemize—and to do that, you’ve gotta pile up more deductions in one year.

Three Winning Ways to Get Your Charitable Giving Counted

1. Bunching Contributions

Don’t drip your generosity year by year—bundle it. Let’s say you normally donate $10,000 a year. Instead, give $30,000 in one year. That extra bulk pushes you above the standard deduction, letting you itemize. For the next two years, take the standard deduction again.

Pros:

• Unlocks extra tax deduction for that big year.
• Simple, easy to understand.

Cons:

• The more you overshoot the standard deduction, the less efficient each dollar gets.
• Your church, or favorite cause, might miss you the next two Decembers (but your bank account won’t).

2. Donor-Advised Funds (DAFs)

A DAF is like a charitable wallet with wings. You pop in a lump sum (say, that $30,000 from our example), get the deduction THIS year, and then dole out $10,000 a year to your favorite causes.

Bonus round: You can invest the DAF money while it waits to be donated. If the market plays nice, your generosity grows.

Caution: Markets sometimes sneeze when you want them to sing. A three-year window is wild territory in investing.

3. Qualified Charitable Distributions (QCDs)—For the 70½ Club

Hit 70½ years old and suddenly you can send money STRAIGHT from your IRA to a charity. This counts towards your required minimum distributions (RMDs), so you don’t pay taxes on it.

Why does this rule matter? Because RMDs force you to withdraw money from your retirement savings, whether you want to or not. Normally, you’d get taxed to the moon, but a QCD lets you sidestep that.

Key wins for QCDs:

• Nixes taxable income from RMDs (so your Social Security and Medicare bills don’t go wild).
• Protects your bank balance since you’re giving pre-tax money, instead of hard-earned after-tax dollars.

Be aware: RMDs now start around age 75 for most, but QCDs are still allowed from 70½. Yep, the tax code is confused, too. Use it to your advantage.

Recap Table: Charitable Giving Power Moves

Strategy	Who Should Use	Big Benefit
Bunching	Anyone who donates	Pushes over the standard deduction
Donor-Advised Fund	Planners & investors	Upfront deduction, donate over time
QCD (70½+ IRA)	Retirees with IRAs	Reduces RMD tax, easy giving

Tip: When donating to a DAF, use investments with big gains (low basis). That way, you dodge the capital gains tax, too.

Watch Out for Tax Surcharges: NIIT and Medicare

Think you’re safe now that you’re past the “regular” tax brackets? Hate to break it to you, but there are stealth taxes that hit high earners like a ninja in the night. Time to check the fine print!

Meet the Surcharges: NIIT and the Medicare Surtax

Two bad boys to know:

• 3.8% Net Investment Income Tax (NIIT): If your adjusted gross income is above $250,000 (joint) or $200,000 (single), this tax applies to your investment income. Dividends, capital gains, rental income, you name it.
• 0.9% Extra Medicare Tax: Once you cross the same income lines, the government wants a little more for Medicare. This only hits earned income, like salary or self-employment pay.

It’s sneaky. You don’t see it until the 1040 comes back with a bill higher than expected.

How Much Could These Cost You?

Let’s put it bluntly: Not watching these surcharges can bump your total tax rate higher than you thought. If you’re already sitting near the top, these can take a bite out of that investment growth or your next end-of-year bonus.

How Do You Dodge or Lower Surcharges?

• Load up on municipal bonds. The interest is (usually) tax-free at the federal level, and sometimes at the state level, too. Uncle Sam can’t touch it.
• Watch your year-end dividends and capital gain distributions from your investment accounts. If possible, time sales to stay just under the next income threshold.
• Remember, the Alternative Minimum Tax (AMT) may affect a few of you, but it’s less likely than these surcharges.

Tracking these surprise taxes isn’t fun, but just knowing they exist means you’re already ahead of most folks. The best defense is good record keeping and a little eye on the scoreboard as December approaches.

Roth Conversions: A Powerful Strategy During Lower Income Years

Let’s talk about Roth conversions. It’s the secret tunnel from your traditional IRA or 401(k) into a Roth—where future growth and withdrawals are tax-free. You heard me right, tax. Free.

So What’s a Roth Conversion?

Simple: You tell your pre-tax retirement account, “I’m done waiting.” Move some (or all) into a Roth IRA, pay taxes now on that chunk, and—cue the drumroll—never pay a penny of tax on those dollars or the investment growth inside again.

When’s the Right Time?

Here’s the little-known trick: The golden period is after you retire, but before you hit RMD age (around 75 for most people). In those years, your income likely drops, so you can convert chunks of pre-tax money at much lower rates. Think 10% to 20% bracket territory instead of 35% or 37%.

Earlier in your career, this can make sense during sabbaticals, part-time years, or any time your salary takes a short vacation.

Don’t be the person who waits, misses this window, and then sees their RMDs push them right back into sky-high tax brackets!

Why It Works

• Reduces Future RMDs: Less pre-tax money means smaller forced withdrawals (which means less taxable income each year after 75).
• Tax-Free for Life: Once it’s in the Roth, that money and its growth are yours—tax man can’t touch it.
• Opens Up Big Lifetime Savings: Do it right, and you’re talking six figures, sometimes even seven-figure tax bills avoided over your lifetime.

Tactics and Cautions

• Do your homework. Calculating the perfect amount to convert means tracking your income, understanding brackets, and timing carefully.
• Loop in a tax pro unless you love poring over IRS worksheets in your free time. Some years you may want to convert more, others less.
• Act before RMDs sneak up. By the time Uncle Sam is forcing withdrawals, the best Roth conversion tax rates may be gone.

Closing Notes:

These ideas are powerful, but they’re general. Your situation is unique, and one ninja move for your friend could be a disaster for you. Please, talk to a CPA or financial advisor before making big changes.

Remember, your money should work as hard as you do. Catch you next time with even more ways to build, keep, and enjoy your wealth!